1,4,5,8-tetrasubstituted dihydroanthracene-based triptycene trisquinones: Synthesis, structural, and physicochemical characterization

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications Pub Date : 2024-08-02 DOI:10.1080/00397911.2024.2381074

Chang-Seok Hyun , Joohwan Eo , Ji Eon Kwon , Byeong-Kwan An

引用次数: 0

Abstract

1,4,5,8-tetrasubstituted dihyroanthracene-based triptycene trisquinones (TT) molecules, THAO-TT and tris(THAO)-TT, were synthesized by Diels–Alder reaction between TT and 1,4,5,8-tetrakis(hexyloxy)anthracene to produce the extended triptycene derivatives containing electron-accepting functionality. The prepared THOA-TT and tris(THOA)-TT exhibited excellent thermal stability owing to the rigid TT framework. The optical and redox properties of THOA-TT and tris(THOA)-TT were controlled by the homoconjugation between the benzoquinone units and the peripheral units through the connecting methine groups.

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1,4,5,8-四取代二氢蒽基三庚烯三醌：合成、结构和理化特性分析

通过 TT 与 1,4,5,8-四(己氧基)蒽之间的 Diels-Alder 反应合成了 1,4,5,8-四取代二氢蒽基三庚烯三醌（TT）分子 THAO-TT 和 tris(THAO)-TT，从而制备出含有电子接受官能团的扩展三庚烯衍生物。制备的 THOA-TT 和三(THOA)-TT 具有良好的热稳定性，这得益于 TT 的刚性框架。THOA-TT 和三(THOA)-TT 的光学和氧化还原特性由苯醌单元和外围单元之间通过连接的甲基进行的同共轭控制。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Synthetic Communications 化学-有机化学

CiteScore

4.40

自引率

4.80%

发文量

156

审稿时长

4.3 months

期刊介绍： Synthetic Communications presents communications describing new methods, reagents, and other synthetic work pertaining to organic chemistry with sufficient experimental detail to permit reported reactions to be repeated by a chemist reasonably skilled in the art. In addition, the Journal features short, focused review articles discussing topics within its remit of synthetic organic chemistry.